arteflene   Click here for help

GtoPdb Ligand ID: 10397

Synonyms: Ro 42-1611
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Arteflene is a synthetic endoperoxide with antimalarial activity. It is derived from yingzhaosu A, a phytochemical endoperoxide isolated from A. uncinatus and structurally unrelated to the artemisinins [2].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 35.53
Molecular weight 408.12
XLogP 4.66
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C1CC2CC(C1C)OOC2(C)C=Cc1ccc(cc1C(F)(F)F)C(F)(F)F
Isomeric SMILES O=C1C[C@H]2C[C@@H]([C@@H]1C)OO[C@@]2(C)/C=C\c1ccc(cc1C(F)(F)F)C(F)(F)F
InChI InChI=1S/C19H18F6O3/c1-10-15(26)8-13-9-16(10)27-28-17(13,2)6-5-11-3-4-12(18(20,21)22)7-14(11)19(23,24)25/h3-7,10,13,16H,8-9H2,1-2H3/b6-5-/t10-,13+,16+,17+/m1/s1
InChI Key LRTRTVPZZJAADL-DAHZFVMQSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Fernández-Álvaro E, Hong WD, Nixon GL, O'Neill PM, Calderón F. (2016)
Antimalarial Chemotherapy: Natural Product Inspired Development of Preclinical and Clinical Candidates with Diverse Mechanisms of Action.
J Med Chem, 59 (12): 5587-603. [PMID:26791529]
2. Hofheinz W, Bürgin H, Gocke E, Jaquet C, Masciadri R, Schmid G, Stohler H, Urwyler H. (1994)
Ro 42-1611 (arteflene), a new effective antimalarial: chemical structure and biological activity.
Trop Med Parasitol, 45 (3): 261-5. [PMID:7899801]
3. Jaquet C, Stohler HR, Chollet J, Peters W. (1994)
Antimalarial activity of the bicyclic peroxide Ro 42-1611 (arteflene) in experimental models.
Trop Med Parasitol, 45 (3): 266-71. [PMID:7899802]